Difference between revisions of "Acetylene"

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[[File:Acetylene.png|thumb|301x301px]]
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'''Acetylene''' (or '''ethyne''') is a flammable gas used in welding and making explosives. It contains a triple bond between two carbons in its structure, making it the simplest [[alkyne]], and has the formula C<sub>2</sub>H<sub>2</sub>.  
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| Name = Acetylene
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| Reference =
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| IUPACName = Acetylene
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| PIN = Acetylene
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| SystematicName = Ethyne
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| OtherNames =
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| ImageFile1 = Solid acetylene subliming by ChemicalForce.jpg
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| ImageCaption1 = Solid acetylene, subliming at room temperature
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| Section1 = {{Chembox Identifiers
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless gas
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| BoilingPt =
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| BoilingPtC = −84
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| BoilingPt_ref =
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| BoilingPt_notes = (sublimes)
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| Density = 1.097 g/cm<sup>3</sup>
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| Formula = C<sub>2</sub>H<sub>2</sub>
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| HenryConstant =
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| LogP =
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| MolarMass = 26.04 g/mol
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| MeltingPt =
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| MeltingPtC = −80.8
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| MeltingPt_notes =
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| Odor = Slight ethereal odor
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| pKa = 25
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| pKb =
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| Solubility = 1.2 g/L (25 °C)
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| SolubleOther = Soluble in [[acetone]], [[benzene]], [[chloroform]], [[diethyl ether]], [[dimethylformamide]]<br>Slightly soluble in glacial [[acetic acid]], [[carbon disulfide]], [[ethanol]]
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| VaporPressure = 44.2 atm (20 °C)
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| MolShape = Linear
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| DeltaGf =
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| DeltaHc =
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| DeltaHf = 226.88 kJ/mol
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| Entropy = 201 J·mol<sup>−1</sup>·K<sup>−1</sup>
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 300 °C (572 °F; 573 K)
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| ExploLimits = 2.5-100%
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| ExternalMSDS = [http://www.praxair.com/-/media/documents/sds/acetylene/acetylene-gas-c2h2-safety-data-sheet-sds-p4559.pdf PRAXAIR]
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| MainHazards = Flammable<br>Explosive
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'''Acetylene''' (or '''ethyne''') is a flammable gas used in welding and making explosives. It contains a triple bond between two carbons in its structure, making it the simplest [[alkyne]], and has the formula '''C<sub>2</sub>H<sub>2</sub>'''.  
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
 
Acetylene burns in oxygen with a very hot and bright flame, with a temperature of 2534 °C at atmospheric pressure. The temperature can be higher if [[nitrous oxide]] is used.
 
Acetylene burns in oxygen with a very hot and bright flame, with a temperature of 2534 °C at atmospheric pressure. The temperature can be higher if [[nitrous oxide]] is used.
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: C<sub>2</sub>H<sub>2</sub> + 5/2 O<sub>2</sub> → 2 CO<sub>2</sub> + H<sub>2</sub>O
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: C<sub>2</sub>H<sub>2</sub> + 5 N<sub>2</sub>O → 2 CO<sub>2</sub> + H<sub>2</sub>O + 5 N<sub>2</sub>
  
 
It will ignite on contact with [[chlorine]] at standard conditions.
 
It will ignite on contact with [[chlorine]] at standard conditions.
  
−
Acetylene is used to make the explosives [[copper(I) acetylide]] and [[silver acetylide]]. These are both rather sensitive and moderately powerful primary explosives.  
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Acetylene is used to make the explosives [[copper(I) acetylide]] and [[silver acetylide]]. These are both rather sensitive and moderately powerful primary explosives.
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 +
: C<sub>2</sub>H<sub>2</sub> (g) + 2 CuCl (s) → Cu<sub>2</sub>C<sub>2</sub> (s) + 2 HCl (g)
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: C<sub>2</sub>H<sub>2</sub> (g) + 2 AgNO<sub>2</sub> (s) → Ag<sub>2</sub>C<sub>2</sub> (s) + 2 HNO<sub>3</sub> (aq)
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[[Formaldehyde]] will react with acetylene gas in water, in the presence of copper(I) acetylide to form 1,4-butynediol.<ref>https://www.youtube.com/watch?v=ljgtaEO3OVY</ref>
  
 
Acetylene reacts with the [[amide]]s of alkali metals while in ammonia solution to form water-soluble alkali metal acetylides.  
 
Acetylene reacts with the [[amide]]s of alkali metals while in ammonia solution to form water-soluble alkali metal acetylides.  
 +
 
===Physical===
 
===Physical===
 
Acetylene cannot exist as a liquid at any temperature under normal pressures, and it is extremely inadvisable to pressurize the gas due to the high risk of an explosion. Industrially, cylinders of acetylene are filled with a porous inert sponge to avoid having high pressures of the gas. This sponge is filled with [[acetone]] or [[dimethylformamide]], in which the the gas dissolves.
 
Acetylene cannot exist as a liquid at any temperature under normal pressures, and it is extremely inadvisable to pressurize the gas due to the high risk of an explosion. Industrially, cylinders of acetylene are filled with a porous inert sponge to avoid having high pressures of the gas. This sponge is filled with [[acetone]] or [[dimethylformamide]], in which the the gas dissolves.
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Mixtures of acetylene and air are extremely explosive, with acetylene volumes from 2.6% to 80% capable of detonating.  
 
Mixtures of acetylene and air are extremely explosive, with acetylene volumes from 2.6% to 80% capable of detonating.  
  
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While acetylene itself may not have an odor, any cylinder of the gas will contain a small amount of an odorant, and the gas generated from [[calcium carbide]] and water always has a strong smell due to impurities.  
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While acetylene itself may not have an odor, any cylinder of the gas will contain a small amount of an odorant, and the gas generated from [[calcium carbide]] and water always has a strong smell due to impurities.
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==Availability==
 
==Availability==
 
Cylinders of acetylene are available generally at welding supply stores. There is a consumer use for cylinders of this gas.   
 
Cylinders of acetylene are available generally at welding supply stores. There is a consumer use for cylinders of this gas.   
  
 
==Preparation==
 
==Preparation==
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In a home chemistry setting, acetylene is generated by the reaction of [[calcium carbide]] and water. The calcium carbide used is often a low grade, so it will produce a variety of other gases such as[[Hydrogen sulfide| hydrogen sulfide]] and [[phosphine]].
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In a home chemistry setting, acetylene is generated by the reaction of [[calcium carbide]] and [[water]].
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: CaC<sub>2</sub> + 2 H<sub>2</sub>O → Ca(OH)<sub>2</sub> + C<sub>2</sub>H<sub>2</sub>
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The calcium carbide used is often a low grade, so it will produce a variety of other gases such as[[Hydrogen sulfide| hydrogen sulfide]] and [[phosphine]].
  
 
To increase the purity of acetylene from calcium carbide, the gas can be lead through a wash bottle containing [[sodium hydroxide]], then plain water to remove any sodium hydroxide.
 
To increase the purity of acetylene from calcium carbide, the gas can be lead through a wash bottle containing [[sodium hydroxide]], then plain water to remove any sodium hydroxide.
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==Projects==
 
==Projects==
 
[[File:Copper-acetylide-16.jpg|thumb|282px|Copper Acetylide - Chemistry-chemists.com]]
 
[[File:Copper-acetylide-16.jpg|thumb|282px|Copper Acetylide - Chemistry-chemists.com]]
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*[[Copper(I) acetylide]]
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*Synthesis of metallic acetylides ([[copper(I) acetylide]], [[silver acetylide]], etc.)
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*[[Silver acetylide]]
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*Synthesis of 1,4-butynediol
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*Make cyclooctatetraene
  
 
==Handling==
 
==Handling==
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Although unlikely, acetylene can form very sensitive explosives on contact with [[copper]], so the use of copper piping is inadvisable.  
 
Although unlikely, acetylene can form very sensitive explosives on contact with [[copper]], so the use of copper piping is inadvisable.  
  
−
While generally not terrible toxic when pure, if generated from calcium carbide, many other gases toxic like [[hydrogen sulfide]] may be produced.
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While generally not terrible toxic when pure, if generated from technical-grade calcium carbide, many other gases toxic like [[hydrogen sulfide]] or [[phosphine]] may be produced.
  
 
===Storage===
 
===Storage===
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==References==
 
==References==
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<span style="color:rgb(68,68,68);font-family:arial,sans-serif;font-size:13px;line-height:normal;white-space:nowrap;">'Encyclopedia of Explosives and Related Items' - Fedoroff, Vol 1/10. </span>
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*'Encyclopedia of Explosives and Related Items' - Fedoroff, Vol 1/10.
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*http://en.wikipedia.org/wiki/Acetylene
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<span style="line-height:normal;white-space:nowrap;">http://en.wikipedia.org/wiki/Acetylene</span>
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<references/>
 
<references/>
 +
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=8598 Acetylene Synth]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=19576 Cyclicization of Acetylene]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=270 Acetylene trimerization to Benzene]
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
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[[Category:Hydrocarbons]]
 
[[Category:Alkynes]]
 
[[Category:Alkynes]]
 
[[Category:Gases]]
 
[[Category:Gases]]
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[[Category:Hydrocarbons]]
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[[Category:Easily prepared chemicals]]

Latest revision as of 22:12, 29 May 2023

Acetylene
Solid acetylene subliming by ChemicalForce.jpg
Solid acetylene, subliming at room temperature
Acetylene.png
Names
IUPAC name
Acetylene
Preferred IUPAC name
Acetylene
Systematic IUPAC name
Ethyne
Properties
C2H2
Molar mass 26.04 g/mol
Appearance Colorless gas
Odor Slight ethereal odor
Density 1.097 g/cm3
Melting point −80.8 °C (−113.4 °F; 192.3 K)
Boiling point −84 °C (−119 °F; 189 K) (sublimes)
1.2 g/L (25 °C)
Solubility Soluble in acetone, benzene, chloroform, diethyl ether, dimethylformamide
Slightly soluble in glacial acetic acid, carbon disulfide, ethanol
Vapor pressure 44.2 atm (20 °C)
Acidity (pKa) 25
Thermochemistry
201 J·mol−1·K−1
226.88 kJ/mol
Hazards
Safety data sheet PRAXAIR
Related compounds
Related compounds
 Ethene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetylene (or ethyne) is a flammable gas used in welding and making explosives. It contains a triple bond between two carbons in its structure, making it the simplest alkyne, and has the formula C2H2.

Properties

Chemical

Acetylene burns in oxygen with a very hot and bright flame, with a temperature of 2534 °C at atmospheric pressure. The temperature can be higher if nitrous oxide is used.

C2H2 + 5/2 O2 → 2 CO2 + H2O
C2H2 + 5 N2O → 2 CO2 + H2O + 5 N2

It will ignite on contact with chlorine at standard conditions.

Acetylene is used to make the explosives copper(I) acetylide and silver acetylide. These are both rather sensitive and moderately powerful primary explosives.

C2H2 (g) + 2 CuCl (s) → Cu2C2 (s) + 2 HCl (g)
C2H2 (g) + 2 AgNO2 (s) → Ag2C2 (s) + 2 HNO3 (aq)

Formaldehyde will react with acetylene gas in water, in the presence of copper(I) acetylide to form 1,4-butynediol.[1]

Acetylene reacts with the amides of alkali metals while in ammonia solution to form water-soluble alkali metal acetylides.

Physical

Acetylene cannot exist as a liquid at any temperature under normal pressures, and it is extremely inadvisable to pressurize the gas due to the high risk of an explosion. Industrially, cylinders of acetylene are filled with a porous inert sponge to avoid having high pressures of the gas. This sponge is filled with acetone or dimethylformamide, in which the the gas dissolves.

Mixtures of acetylene and air are extremely explosive, with acetylene volumes from 2.6% to 80% capable of detonating.

While acetylene itself may not have an odor, any cylinder of the gas will contain a small amount of an odorant, and the gas generated from calcium carbide and water always has a strong smell due to impurities.

Availability

Cylinders of acetylene are available generally at welding supply stores. There is a consumer use for cylinders of this gas.

Preparation

In a home chemistry setting, acetylene is generated by the reaction of calcium carbide and water.

CaC2 + 2 H2O → Ca(OH)2 + C2H2

The calcium carbide used is often a low grade, so it will produce a variety of other gases such as hydrogen sulfide and phosphine.

To increase the purity of acetylene from calcium carbide, the gas can be lead through a wash bottle containing sodium hydroxide, then plain water to remove any sodium hydroxide.

Projects

Copper Acetylide - Chemistry-chemists.com

Handling

Safety

Explosions of acetylene can be very powerful. It is easily capable of detonation when pressurized, and is quite shock sensitive, meaning shock waves generated from explosives could set it off. Fuel/air mixtures can ignite very easily and will detonate or burn very hot and bright.

Although unlikely, acetylene can form very sensitive explosives on contact with copper, so the use of copper piping is inadvisable.

While generally not terrible toxic when pure, if generated from technical-grade calcium carbide, many other gases toxic like hydrogen sulfide or phosphine may be produced.

Storage

Acetylene is stored commercially in cylinders, where it is dissolved in acetone or dimethylformamide (DMF), contained in a gas cylinder with a porous filling (Agamassan).

A new method was developed in 2009, where acetone is stored in a metal-organic framework (MOF), a lattice-like structure made of copper oxide and benzene.[2]

Disposal

Acetylene can be safely released in the atmosphere or burned.

References

  1. ↑ https://www.youtube.com/watch?v=ljgtaEO3OVY
  2. ↑ http://pubs.acs.org/doi/abs/10.1021/ja904782h

Relevant Sciencemadness threads

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